The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones: A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts
Abstract
Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride with triethylamine by the promotion of a basic catalyst such as 4-(dimethylamino)pyridine. A variety of lactones are also prepared in high yields at room temperature from the corresponding omega-hydroxycarboxylic acids with use of 2-methyl-6-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine. A similar reaction occurs with triethylamine when using a catalytic amount of 4-(dimethylamino)pyridine 1-oxide as an effective promoter for the intramolecular condensation reaction. These methods are successfully applied to the synthesis of erythro-aleuritic acid lactone and an eight-membered-ring lactone moiety of octalactins A and B. The efficiency of the cyclizations is compared to those of other reported lactonizations.
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Citations
Cites
Manabe, K., Sun, X.-M., & Kobayashi, S. (2001) · Journal of the American Chemical Society · doi:10.1021/ja016338q · Cited by 215
Cited by
Shiina, I. (2007) · Chemical Reviews · doi:10.1021/cr050045o · Cited by 346
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Metadata
- Authors
- Shiina, I., Kubota, M., Oshiumi, H., & Hashizume, M.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-02-10
- Volume
- 69
- Issue
- 6
- Pages
- 1822-1830
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2104516185
- Cited by
- 416
- References
- 1
- FWCI
- 9.53
- Type
- journal article
- Language
- en
- Open access
- closed
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